US4093642A - Surface active silicones - Google Patents
Surface active silicones Download PDFInfo
- Publication number
- US4093642A US4093642A US05/752,879 US75287976A US4093642A US 4093642 A US4093642 A US 4093642A US 75287976 A US75287976 A US 75287976A US 4093642 A US4093642 A US 4093642A
- Authority
- US
- United States
- Prior art keywords
- matter
- composition
- chohch
- carbon atoms
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920001296 polysiloxane Polymers 0.000 title abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 23
- -1 siloxane compounds Chemical class 0.000 claims abstract description 22
- 125000000129 anionic group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 150000003839 salts Chemical class 0.000 abstract description 7
- 150000003961 organosilicon compounds Chemical class 0.000 abstract description 4
- 238000005649 metathesis reaction Methods 0.000 abstract description 3
- 125000001453 quaternary ammonium group Chemical class 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 101150108015 STR6 gene Proteins 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical class C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940067741 sodium octyl sulfate Drugs 0.000 description 1
- XZTJQQLJJCXOLP-UHFFFAOYSA-M sodium;decyl sulfate Chemical compound [Na+].CCCCCCCCCCOS([O-])(=O)=O XZTJQQLJJCXOLP-UHFFFAOYSA-M 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
Definitions
- siloxane compounds containing anions and cations have been made.
- such compounds have been formed by proton (hydrogen ion) transfer from an acid group to an amine group or one of the ions has not been surface active.
- the compounds have not been stable to pH changes or have had ions that essentially dilute the surface activity of the compound.
- U.S. Pat. No. 3,389,160 discloses dialkylamino hydroxy organosilicon salts of carboxylic acids of one to six carbon atoms, and it also discloses quaternary ammonium halide derivatives of dialkylamino hydroxy organsilicon compounds.
- the dialkylamino hydroxy organosilicon salts of carboxylic acids disclosed in that patent are formed by proton transfer.
- the quaternary ammonium halide derivatives of dialkylamino hydroxy organosilicon compounds of that patent have halide anions that are not surface active.
- U.S. Pat. No. 3,303,048 discloses aminoalkylsiloxane salts of carboxylic acids such as decoic, oleic, and stearic acids.
- the siloxane salts of that patent are also formed by proton transfer from an acid group to an amine group.
- British Pat. No. 1,056,066 discloses oxypropylated triethanolamine salts of siloxane carboxylic acids derived from the hydrolysis of addition products of maleic anhydride and hydroxysiloxanes. Again, this patent discloses siloxane salts formed by proton transfer from an acid group to an amine group.
- U.S. Pat. No. 3,278,465 discloses a broad class of siloxanes containing ion pairs as surfactants in the manufacture of cellular polyurethanes.
- none of the silicon-free counterions in the specifically disclosed siloxanes are surface active.
- no disclosure is made of the advantage inherent in polysiloxanes containing ion pairs wherein both ion and counterion are surface active.
- This invention relates to novel organosilicon compounds containing surface-active anionic and cationic substituents. These compounds are formed by metathesis reactions between metallic salts of anionic silicone or organic surface-active compounds and halide salts of quaternary ammonium silicone or organic surface-active compounds.
- the novel compounds fall into two classes.
- R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms
- R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms,
- XX - is a divalent anionic group covalently bonded to R' and ionically bonded to Y + ,
- y + is a monovalent cation that has at least 8 carbon atoms and that is derived from a cationic surfactant having a halogen counterion by removal of the halogen, and that is free of ionically-bonded hydrogen,
- m is an integer having a value from 1 to 100 (preferably from 1 to 5),
- n is an integer having a value from 0 to 200 (preferably from 0 to 10), and
- the ratio of m to (n+2) being at least 0.1 to 20 (preferably at least 0.1 to 0.5).
- R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms
- R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms,
- YY + is a divalent cationic group that is free of ionically-bonded hydrogen and that is covalently bonded to R' and ionically bonded to X - ,
- x - is a monovalent anion that has at least 8 carbon atoms and that is derived from an anionic surfactant having a monovalent metal counterion by removal of the metal,
- m is an integer having an average value from 1 to 100 (preferably from 1 to 5),
- n is an integer having a value from 0 to 200 (preferably from 0 to 10), and
- the ratio of m to (n+2) being at least 0.1 to 20 (preferably at least 0.1 to 0.5).
- Suitable monovalent hydrocarbon groups represented by R in Formulas I and II above include alkyl, alkenyl, aryl, alkaryl, or aralkyl groups.
- Illustrative monovalent hydrocarbon groups from which R can be selected are: methyl, ethyl, propyl, isobutyl, decyl, octadecyl, cyclopentyl, cyclohexyl, naphthyl, vinyl, butenyl, cyclohexenyl, tolyl, xylyl, benzyl and betaphenylethyl.
- R is methyl.
- Suitable divalent organic radicals represented by R' in Formulas I and II above are the alkylene, arylene or aralkylene radicals; suitable divalent hydrocarbonoxy radicals represented by R' are the same as the hydrocarbon radicals except that they also contain one or more ether lnkages linkages --CH 2 --O--CH 2 --) and/or hydroxyl substituents.
- R' can be an alkylene group such as methylene, ethylene, propylene, 2- methylpropylene or butylene; it can be an arylene group such as phenylene; it can be an aralkylene group such as phenyl methylene or it can be a divalent hydrocarbonoxy radical having the formula
- the monovalent hydrocarbon groups represented by R may be the same or different on each siloxane moiety.
- these hydrocarbon groups may be the same or different with respect to different siloxane moieties within the same compound.
- suitable monovalent cations represented by Y + include Me 3 N +R (e.g. Me 3 N + C 12 H 25 ) and R 4 N + (e.g. (C 12 H 25 ) 4 N + ) wherein R is defined above, with the proviso that at least one R group in each cation have at least 8 carbon atoms.
- suitable monovalent cations include the class of cations represented by the formula: ##STR3## wherein R, R', YY + and n are defined in Formula II above. -
- suitable monovalent anions represented by X - include - O 2 CR (e.g., --O 2 C 8 H 17 ) and - O 4 SR (e.g., - O 4 SC 8 H 17 , - O 4 SC 10 H 21 , - O 4 SC 12 H 25 ) wherein R is defined above, with the proviso that at least one R group in each anion have at least 8 carbon atoms.
- suitable monovalent anions include the class of anions represented by the formula: ##STR4## wherein R, R', XX - and n are defined in Formula II above.
- Suitable divalent cationic groups represented by YY + include + NR 3 (such as + NMe 3 ) wherein R is defined above; ##STR5##
- the compounds of this invention are ion-pair containing compounds in which each of the substituents is a surfactant and can be either silicone or organic.
- novel organosilicon compounds of the invention are formed by metathesis reactions between metallic salts of anionic silicone or organic surface-active compounds and halide salts of quaternary ammonium silicone or organic surface-active compounds.
- the compounds of the instant invention are not formed by proton transfer and neither ion in the ion pair contains acidic protons.
- the process of forming the compounds of the invention as given in Formulas I and II above is illustrated below using specific reactants: ##STR6##
- the process of the invention is performed by combining equimolar amounts of the respective ionic reactants in the presence of solvents.
- the solvents used may be water miscible, such as low molecular weight alcohols and acetone, or water may be used as the sole solvent. When water alone is used, the product may precipitate and be isolated by filtration. Otherwise, the more volatile solvents are stripped and the residue is extracted with an organic solvent immiscible with water such as ethyl ether, chloroform, carbon tetrachloride, benzene or toluene. Water may be added to aid in phase separation and removal of inorganic salts. The extraction solutions are then filtered and solvent stripped, leaving products in the form of waxy solids or very viscous semi-solids.
- temperatures may be used in the process of the invention, ranging from 0° to 200° C, there is no advantage to the use of high or low temperatures. Therefore, room temperature is the preferred temperature for the process of the invention. Atmospheric pressure is used unless low boiling solvents are used.
- the process of this invention is applicable to any silicone or organic, anionic or cationic, surfaceactive reactants.
- the compounds of the instant invention are useful in solution using aqueous and non-aqueous solvents. Therefore, it is not necessary to isolate the compositions of the invention. Instead, the compounds of the invention can be used in the solutions in which they are prepared. Since the compounds of the invention are useful in the presence of the surface-inactive metallic halide by-products of the invention, it is not necessary to remove these halides from solution.
- organosilicon compounds of the present invention are useful as aqueous surface tension depressants, having limiting surface tensions in water of 20.8 to 22.5 dyne/cm. with very low critical micelle concentrations of 0.0005 to 0.05 weight percent. At these low concentrations they are much more effective aqueous surface tension depressants than conventional ionic silicone or organic surfactants.
- the compounds of the invention are potentially useful in a wide variety of other surface related areas such as water-washable lubricants, mold release agents, wetting agents, bactericides, detergent additives, foam stabilizers, anti-static agents, and as additives to coatings, paints and polishes.
- the compounds of the invention have shown effectiveness as emulsifiers for water-hydrocarbon, water-halocarbon, and water-silicone oil mixtures.
- surfactant denotes a material that lowers the bulk surface tension of water to below 40 dynes per centimeter at a concentration of 0.1 parts by weight or lower of the material per 100 parts of water at 25° C.
- surfactants appear in A. M. Schwartz and J. W. Perry, Surface Active Agents, Vol. 1, p. 282 (1949).
- Me denotes the methyl group
- g denotes grams
- % denotes weight percent
- the product had a limiting aqueous surface tension of 22.2 dyne/cm.
- the product had a limiting aqueous surface tension of 20.7 dyne/cm. and a critical micelle concentration of 0.02 wt. percent.
- a mixture of 10 ml. of water, 10 ml. of benzene, and 0.2 g. of product formed an emulsion when shaken which was stable for several days.
- the product also acted as an emulsifying agent for water-silicone oil and water-CCl 4 .
- the product had a limiting aqueous surface tension of 20.8 dyne/cm, and a critical micelle concentration 0.04 wt. %.
- the product was a clear tan solid having the formula (Me 3 SiO) 2 MeSi(CH 2 ).sub. 3 OCH 2 CHOHCH 2 + NMe 3 - O 3 SCH 2 CH 2 N(CH 3 )CH 2 CHOHCH 2 O(CH 2 ) 3 SiMe(OSiMe 3 ) 2 .
- the product had a limiting aqueous surface tension of 21.2 dyne/cm., and it was an effective emulsifying agent at 0.5 wt. % for equal volumes of benzene and water.
- the product was a clear tan paste having the formula: (Me 3 SiO) 2 MeSi(CH 2 ) 3 OCH 2 CHOHCH 2 + NMe 3 -O 4 SC 10 H 21 .
- the product had a limiting aqueous surface tension of 21.8 dyne/cm.
- a polycationic silicone fluid Me 3 SiO (Me 2 SiO) 180 (MeYSiO) 20 SiMe 3 , were Y is -- (CH 2 ) 3 OCH 2 CH 2 .sup. ⁇ NMe 3 .sup. ⁇ I, (13.1 g.) was dissolved in 40 ml. dry ethanol. The ethanol solution was combined with a solution of 3.8 g. sodium dodecyl sulfate (C 12 H 25 SO 4 Na) in 20 ml. 50% aqueous ethanol. The combined solution was stirred, and 175 ml. H 2 O added, causing the precipitation of an oily solid.
- This polyfunctional ion-pair product was insoluble in pure water, reflecting its higher molecular weight. It was effective as an emulsifier for water-halocarbon and water-silicone oil mixtures.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
Description
--(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 -- or --(CH.sub.2).sub.3 O(CH.sub.2).sub.3 --.
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/752,879 US4093642A (en) | 1976-12-20 | 1976-12-20 | Surface active silicones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/752,879 US4093642A (en) | 1976-12-20 | 1976-12-20 | Surface active silicones |
Publications (1)
Publication Number | Publication Date |
---|---|
US4093642A true US4093642A (en) | 1978-06-06 |
Family
ID=25028273
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/752,879 Expired - Lifetime US4093642A (en) | 1976-12-20 | 1976-12-20 | Surface active silicones |
Country Status (1)
Country | Link |
---|---|
US (1) | US4093642A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2948760A1 (en) * | 1978-12-05 | 1980-06-19 | Oreal | SURFACE-ACTIVE POLYSILOXANES, METHOD FOR THE PRODUCTION THEREOF AND AGENTS CONTAINING THESE COMPOUNDS |
US4918210A (en) * | 1987-01-20 | 1990-04-17 | Fenton William N | Zwitterionic polysiloxane compositions |
US5200488A (en) * | 1990-11-06 | 1993-04-06 | Sagami Chemical Research Center | Polyorganosiloxane having a quaternary salt at its one terminal and percutaneous absorption-promoting agent |
DE4224136C1 (en) * | 1992-07-22 | 1993-07-15 | Th. Goldschmidt Ag, 4300 Essen, De | |
US6579923B2 (en) * | 2001-02-05 | 2003-06-17 | 3M Innovative Properties Company | Use of a silicone surfactant in polishing compositions |
US20090176893A1 (en) * | 2007-12-26 | 2009-07-09 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified trisiloxane ionic surfactants |
US20090173912A1 (en) * | 2007-12-26 | 2009-07-09 | Momentive Performance Materials Inc. | Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants |
WO2010110484A1 (en) * | 2009-03-24 | 2010-09-30 | 広栄化学工業株式会社 | Onium salt with (trialkoxysilyl)alkyl group |
CN113620984A (en) * | 2021-09-13 | 2021-11-09 | 山东新港化工有限公司 | Surfactant containing organosilicon group for reducing blood pressure and increasing injection, and preparation method and application thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3278465A (en) * | 1962-06-28 | 1966-10-11 | Ici Ltd | Manufacture of cellular polyurethane materials in the presence of a polysiloxane stabilizer |
US3389160A (en) * | 1964-07-14 | 1968-06-18 | Union Carbide Corp | Dialkylamino hydroxy organosilicon compounds and derivatives thereof |
US4006176A (en) * | 1975-04-22 | 1977-02-01 | The Procter & Gamble Company | Organosilane compounds |
-
1976
- 1976-12-20 US US05/752,879 patent/US4093642A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3278465A (en) * | 1962-06-28 | 1966-10-11 | Ici Ltd | Manufacture of cellular polyurethane materials in the presence of a polysiloxane stabilizer |
US3389160A (en) * | 1964-07-14 | 1968-06-18 | Union Carbide Corp | Dialkylamino hydroxy organosilicon compounds and derivatives thereof |
US4006176A (en) * | 1975-04-22 | 1977-02-01 | The Procter & Gamble Company | Organosilane compounds |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2948760A1 (en) * | 1978-12-05 | 1980-06-19 | Oreal | SURFACE-ACTIVE POLYSILOXANES, METHOD FOR THE PRODUCTION THEREOF AND AGENTS CONTAINING THESE COMPOUNDS |
FR2443476A1 (en) * | 1978-12-05 | 1980-07-04 | Oreal | NOVEL SURFACTANT POLYSILOXANES, PROCESS FOR PREPARING SAME AND COMPOSITIONS CONTAINING THE SAME |
US4342742A (en) * | 1978-12-05 | 1982-08-03 | L'oreal | Surface-active polysiloxanes |
US4490356A (en) * | 1978-12-05 | 1984-12-25 | L'oreal | Surface-active polysiloxanes |
US4523921A (en) * | 1978-12-05 | 1985-06-18 | L'oreal | Surface-active polysiloxanes |
US4918210A (en) * | 1987-01-20 | 1990-04-17 | Fenton William N | Zwitterionic polysiloxane compositions |
US5200488A (en) * | 1990-11-06 | 1993-04-06 | Sagami Chemical Research Center | Polyorganosiloxane having a quaternary salt at its one terminal and percutaneous absorption-promoting agent |
EP0581082A1 (en) * | 1992-07-22 | 1994-02-02 | Th. Goldschmidt AG | Process for the preparation of surface-active anion-cation complexes |
DE4224136C1 (en) * | 1992-07-22 | 1993-07-15 | Th. Goldschmidt Ag, 4300 Essen, De | |
US6579923B2 (en) * | 2001-02-05 | 2003-06-17 | 3M Innovative Properties Company | Use of a silicone surfactant in polishing compositions |
US20090176893A1 (en) * | 2007-12-26 | 2009-07-09 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified trisiloxane ionic surfactants |
US20090173912A1 (en) * | 2007-12-26 | 2009-07-09 | Momentive Performance Materials Inc. | Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants |
US20110028569A1 (en) * | 2007-12-26 | 2011-02-03 | Leatherman Mark D | Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants |
WO2010110484A1 (en) * | 2009-03-24 | 2010-09-30 | 広栄化学工業株式会社 | Onium salt with (trialkoxysilyl)alkyl group |
JP2010248165A (en) * | 2009-03-24 | 2010-11-04 | Koei Chem Co Ltd | Onium salt having trialkoxysilylalkyl group |
CN113620984A (en) * | 2021-09-13 | 2021-11-09 | 山东新港化工有限公司 | Surfactant containing organosilicon group for reducing blood pressure and increasing injection, and preparation method and application thereof |
CN113620984B (en) * | 2021-09-13 | 2024-03-15 | 山东新港化工有限公司 | Organosilicon group-containing surfactant for reducing pressure and increasing injection, preparation method and application thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2129806C (en) | Silanes with hydrophilic groups, their synthesis and use as surfactants in aqueous media | |
JP2749520B2 (en) | Silane having hydrophilic group and surfactant in aqueous medium comprising the silane | |
US3389160A (en) | Dialkylamino hydroxy organosilicon compounds and derivatives thereof | |
US5091493A (en) | Silicone phosphobetaines | |
US5093452A (en) | Silicone phosphate amines | |
US5401871A (en) | Organopolysiloxane polyethers and their use as hydrolysis-resistant wetting agents in aqueous systems | |
US4093642A (en) | Surface active silicones | |
US3123641A (en) | Cation-active surface active trilower- | |
EP0367381A2 (en) | Carbosilane surfactants | |
US4777277A (en) | Organosilicon sulphosuccinates | |
US4873020A (en) | Fluorochemical surfactants and process for preparing same | |
EP0467852A2 (en) | Perfluoroalkylpolyoxyalkylpolysiloxane surfactants | |
US3856893A (en) | Hybrid ionic phosphorus compounds | |
UST984005I4 (en) | Yellow-dye-forming couplers | |
US3997580A (en) | Silicone sulfates | |
US5068377A (en) | Betaine-containing siloxane compounds and method for making | |
US4814471A (en) | Process for preparing sulphonated organosilicon compounds | |
US5405983A (en) | Silicone modified phospholipid compositions | |
US4836958A (en) | Fluorinated cationic compounds | |
US4673436A (en) | N, S containing corrosion inhibitors | |
GB2116966A (en) | Aqueous compositions of N-oxyalkylated quaternary ammonium salt surfactants | |
US5977189A (en) | C7 -C12 diol and diol alkoxylates as coupling agents for surfactant formulations | |
US5530084A (en) | Organo(poly)siloxane modified with phosphoric ester and process for producing the same | |
GB1439037A (en) | Process for manufacturing aminofunctional polysiloxanes | |
WO1990015797A2 (en) | Quaternized nitrogen containing compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: MORGAN GUARANTY TRUST COMPANY OF NEW YORK, AND MOR Free format text: MORTGAGE;ASSIGNORS:UNION CARBIDE CORPORATION, A CORP.,;STP CORPORATION, A CORP. OF DE.,;UNION CARBIDE AGRICULTURAL PRODUCTS CO., INC., A CORP. OF PA.,;AND OTHERS;REEL/FRAME:004547/0001 Effective date: 19860106 |
|
AS | Assignment |
Owner name: UNION CARBIDE CORPORATION, Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:MORGAN BANK (DELAWARE) AS COLLATERAL AGENT;REEL/FRAME:004665/0131 Effective date: 19860925 |
|
AS | Assignment |
Owner name: CHASE MANHATTAN BANK (N.A.), NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:OSI, SPECIALTIES, INC.;REEL/FRAME:006624/0803 Effective date: 19930708 Owner name: OSI SPECIALTIES, INC. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:UNION CARBIDE CHEMICALS AND PLASTICS CORP.;REEL/FRAME:006633/0206 Effective date: 19930709 |